203900

Bufalin

A cardiotonic steroid isolated from toads of Bufo species that potently inhibits ouabain-sensitive Na⁺,K⁺-ATPase activity (IC₅₀ = 1.4 nM).

• Synonyma: Bufalin, 5β, 20(22)-Bufadienolide-3β, 14-diol
• Empirický vzorec (Hillův zápis): C₂₄H₃₄O₄
• Číslo CAS: 465-21-4
• Molekulová hmotnost: 386.52
• MDL number: MFCD00056525
• UNSPSC Code: 12352211
• NACRES: NA.77

Vlastnosti

• Quality Level: 100
• assay: ≥98% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: white to off-white
• solubility: DMSO: 25 mg/mL; warm ethanol: 25 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: O1C=C(C=CC1=O)[C@@H]2[C@@]3([C@@](C4C([C@@]5([C@@H](C[C@H](CC5)O)CC4)C)CC3)(CC2)O)C
• InChI: 1S/C24H34O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,14,16-20,25,27H,4-5,7-13H2,1-2H3/t16-,17+,18-,19?,20?,22+,23-,24+/m1/s1
• InChI key: QEEBRPGZBVVINN-ZXRSHIDQSA-N

Popis

General description

A cardiotonic steroid isolated from Bufo species toads that potently inhibits ouabain-sensitive Na⁺,K⁺-ATPase activity. Induces apoptosis in various human cell lines such as leukemia HL60 and U937 cells by altering the expression of apoptosis-related genes. Reported to stimulate the activities of p21 activated kinase (PAK) and c-Jun Kinase (JNK) in leukemic cell lines. Induces a transient increase in the expression of Tiam1 mRNA in U937 cell lines (~100 nM). Bufalin also down-regulates gene expression of the intracellular signaling protein 14-3-3 in rat lens, probably a consequence of Na⁺-K⁺-ATPase inhibitors. Reduces the level of topoisomerase II in human leukemia cells.

A cardiotonic steroid isolated from toads of Bufo species that potently inhibits ouabain-sensitive Na⁺,K⁺-ATPase activity (IC₅₀ = 1.4 nM). Induces apoptosis in various human cell lines such as leukemia HL-60 and U937 cells by altering the expression of apoptosis-related genes. Reported to stimulate the activities of p21 activated kinase (PAK) and c-Jun Kinase (JNK) in leukemic cell lines. Induces a transient increase in the expression of Tiam1 mRNA in U937 cell lines (~100 nM). Bufalin also down-regulates gene expression of the intracellular signaling protein 14-3-3 in rat lens, probably a consequence of Na⁺,K⁺-ATPase inhibition. Reduces the level of topoisomerase II in human leukemia cells.

Biochem/physiol Actions

Cell permeable: no

Primary Target
Ouabain-sensitive Na+,K+-ATPase activity

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 1.4 nM against ouabain-sensitive Na+,K+-ATPase activity

Packaging

Packaged under inert gas

Warning

Toxicity: Highly Toxic (H)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.

Kurosawa, M., et al. 2000. Am. J. Physiol.278, C500.
Kawazoe, N., et al. 1999. Oncogene 18, 2413.
McGowan, M.H., et al. 1999. J. Pharmacol. Exp. Ther. 289, 1559.
Watabe, M., et al. 1998. Oncogene 16, 779.
Hashimoto, S., et al. 1997. Leuk. Res. 21, 875.
Morris, J.F., et al. 1997. Comp. Biochem. Physiol. A Physiol. 118, 599.
Brownlee, A.A., et al. 1990. Clin. Sci.78, 169.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Bezpečnostní informace

• pictograms: GHS06
• signalword: Danger
• hcodes: H300
• pcodes: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 2 Oral
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable